Holiday rentals with outdoor seating in Rogers Park, Chicago

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Top-rated rentals with outdoor seating in Rogers Park, Chicago

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Chicago

4.93 out of 5 average rating, 382 reviews

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

6–13 Mar

$123 SGD per night

Guest favourite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 296 reviews

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

2–9 Oct

$189 SGD per night

Superhost

Flat in Chicago

4.83 out of 5 average rating, 190 reviews

Cozy Northside Apt near trains & free St. parking

PRIVATE Entrance, One Bedroom Apt w/ LVG RM near Lake Michigan in beautiful, residential & diverse neighborhood. FREE on street PARKING, OR driveway spot for Addt fee. Sleeps up to 6. *It has a Kitchenette, Full Bath, WiFi, Cable TV, in unit W/D. Close to METRA TRAIN (1 block & 18 min to loop/city center), Bus Stop 1 block & the CTA "L" (elevated) Red Line to City 7 blocks away. Enjoy our proximity to Public Transit, Beaches, Loyola & NW Universities. Great for family, friends & kids.

5–12 Jan

$191 SGD per night

Guest favourite

Guest house in Evanston

4.98 out of 5 average rating, 206 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

28 Mar – 4 Apr

$205 SGD per night

Guest favourite

Guest suite in Andersonville

4.96 out of 5 average rating, 320 reviews

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

28 Dec – 4 Jan

$121 SGD per night

Guest favourite

Flat in Edgewater

4.99 out of 5 average rating, 104 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a bus stop right around the corner and less than 10 miles from the heart of the city, your urban adventure awaits!

7–14 Dec

$195 SGD per night

Guest favourite

Flat in Chicago

4.89 out of 5 average rating, 177 reviews

Historic Chicago neighborhood flat

Private one-bedroom apartment plus queen sleeper sofa in historic Ravenswood Manor. This unit is on the ground floor of a three-flat on a beautiful tree-lined street with plenty of free parking. Close to Brown Line - Francisco Stop - and lots of neighborhood parks. Close to Rockwell and Lincoln Square shopping and restaurants and next to Albany Park, one of Chicago’s most diverse neighborhoods. New fixtures, furniture, appliances, free shared laundry, access to backyard upon request.

1–8 Mar

$148 SGD per night

Guest favourite

Guest suite in Chicago

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

24–31 Oct

$153 SGD per night

Guest favourite

Guest suite in Irving Park

4.99 out of 5 average rating, 137 reviews

BnB on Grace Street - Modern 2-Bedroom Guest Suite

Welcome to Bnb on Grace Street in the charming Old Irving Park neighborhood, in one of the original homes built in 1893! Our private guest suite is modern and recently renovated while highlighting original features of the home such as the exposed brick walls. It's just 2 blocks from a major highway and from the El Train blue line, from which you can travel into downtown or out to O'Hare Airport. The suite includes 2 bedrooms, 1 bathroom, a kitchenette/dining area, and living room.

15–22 Oct

$166 SGD per night

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 483 reviews

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

4–11 Nov

$249 SGD per night

Guest favourite

Apartment in Chicago

4.98 out of 5 average rating, 255 reviews

Northside Chicago Favorite with parking!

Discover this recently renovated, 3-bedroom home offering free on-premises parking and a prime location. Only 3 blocks from Lake Michigan, convenient access to public transportation, express bus to downtown, Navy Pier, and Grant Park (9 miles), and the CTA Jarvis station just 3 blocks away. Close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). Perfect for couples, business travelers, and families.

30 Nov – 7 Dec

$364 SGD per night

Guest favourite

Flat in Lincoln Square

4.96 out of 5 average rating, 323 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Light-filled, comfy 2-bed 1-bath apartment on a quiet, tree-lined street in Lincoln Square on Chicago's north side. Spacious kitchen stocked with essentials, washer/dryer, and your own private porch. Walk to cute local shops, cafes, grocery stores and the Rockwell brown line stop. Pet and kid-friendly (in one of the city's most family-friendly areas). Street parking is free, easy and doesn't require a permit.

18–25 Dec

$176 SGD per night